Instead of the stone wall having been shortened, I'd think the more likely scenario is that the level of the road has been graded and raised, obscuring the lower portion of that cement capped stone wall. Great photos.

That appears to be a single wire telephone. The wire coming down the pole goes into the phone while the wire at the bottom completes the circuit using earth return. OK for short hauls but the noise level increases rapidly with distance. Probably a dedicated service customer protected with padlock.

In addition to being padlocked, the box on the pole has two wire connected to it. One passing around a ceramic insulator and then goes up the pole passing yet another insulator. Another goes straight down to the ground from the bottom of the box. I'd guess this means it's its power and the box may be a junction box or fuse box.

Judging by the porcelain knob and electrical wires running to the box, my guess is there's a switch in the box to turn on a light at the top of the pole.

What is the box used for? Just local messages to people in the neighborhood?

It looks like there are more bike tire tracks on that road than anything else.

[Um, those are wagon tracks. - Dave]

This view seems to be close to the spot in the original image.

The stone wall in the original has been lowered and smoothed over in the current view. But the mall cape in the distance has the same dormers looking out over the roofline, and the outcrop of stones along the edge of the driveway today is also present in the original image.

Sure does seem like the spot. I've commented earlier that "things don't change much in New England." Even more of a truism in coastal Maine.

We see the small sign, Old Ferry Lane, at right. But, past the branches, there is another sign for those headed in this direction. It's a much longer sign. I wonder what it says?

["I'M ACTUALLY A FENCE"? - Dave]

They did a move to the yard back in September. Here is a video from a rail move last year:

Found the spot the photo was taken! Looks like the house is still there as of 2017.
Just love this old photo, makes me want to walk down that dirt road on a nice summer day with my dog.

Railroad fans know of Kittery because it is home to the least active rail line in the country. The line goes to the Portsmouth Naval Shipyard and averages two trains, of just a few cars each, per year. Rumor has it that they carry radioactive waste from submarines to disposal sites in Idaho, but the Navy won't say.